39886-76-5

Basic information

• Product Name: 6-GINGEROL,(+/-)
• Synonyms: rac-[6]-Gingerol
• CAS NO: 39886-76-5
• Molecular Formula: C₁₇H₂₆O₄
• Molecular Weight: 294.388
• Product Categories: Aromatics, Inhibitors, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 39886-76-5.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 453.0±35.0 °C(Predicted)
• Appearance: /
• Density: 1.083±0.06 g/cm3(Predicted)
• PKA: 10.02±0.20(Predicted)
• CAS DataBase Reference: 6-GINGEROL,(+/-)(CAS DataBase Reference)
• NIST Chemistry Reference: 6-GINGEROL,(+/-)(39886-76-5)
• EPA Substance Registry System: 6-GINGEROL,(+/-)(39886-76-5)

Safety Data

• Hazardous Substances Data: 39886-76-5(Hazardous Substances Data)

Usage

Uses

rac-[6]-Gingerol is the racemic mixture of [6]-Gingerol (the active constituent of fresh ginger) and its enantiomer. rac-[6]-Gingerol shows antihepatotoxic effects as well as suppression of spontaneous Ca2+ spikes and isometric contraction.

Upstream product

• 107487-01-4 (5-Pentyl-4,5-dihydro-isoxazol-3-ylmethyl)-phosphonic acid diethyl ester 
• 61871-72-5 (E)-5-hydroxy-1-(4'-hydroxy-3'-methoxyphenyl)-1-decen-3-one 
• 1080-12-2 (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-one 
• 1135-24-6 3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 1186501-32-5 (S,E)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dec-1-en-3-one 
• 60101-00-0 2-Methoxy-1-trimethylsilanyloxy-4-(3-trimethylsilanyloxy-but-3-enyl)-benzene 
• 66-25-1 hexanal 
• 56700-87-9 4-(3-methoxy-4-trimethylsilyloxyphenyl)butan-2-one 
• 23513-14-6 (+/-)-[6]-gingerol 
• 39886-78-7 4-[4-(benzyloxy)-3-methoxyphenyl]butan-2-one 
• 146830-53-7 2-<2-(4-Hydroxy-3-methoxyphenyl)ethyl>-1,3-dithiane 
• 69172-20-9 3-(3-methoxy-4-benzyloxyphenyl)propionaldehyde 
• 92511-73-4 (S)-5-Pentyl-3-((R)-toluene-4-sulfinylmethyl)-4,5-dihydro-isoxazole 

Downstream Products

• 39886-85-6 (3S,5S)-3,5-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)decane 
• 154905-69-8 (3R,5S)-1-(4-hydroxy-3-methoxyphenyl)decane-3,5-diol 
• 555-66-8 [6]-shogaol 
• 23513-13-5 [6]-shogaol 
• 86248-31-9 10-Hydroxy-1-(4-hydroxy-3-methoxy-phenyl)-decan-3-one 
• 1360109-90-5 (4R,6S)-4-(4-(benzyloxy)-3-methoxyphenethyl)-2,2-dimethyl-6-pentyl-1,3-dioxane 
• 1360109-92-7 (3R,5S)-1-(4-(benzyloxy)-3-methoxyphenyl)decane-3,5-diol 
• 1360109-93-8 (3R,5S)-1-(4-(benzyloxy)-3-methoxyphenyl)decane-3,5-diyl diacetate 
• 863780-90-9 (3R,5S)-1-(3,4-dimethoxyphenyl)decane-3,5-diyl diacetate 
• 53254-51-6 (3R,5S)-1-(4-hydroxy-3-methoxyphenyl)decane-3,5-diyl diacetate 
• 39886-76-5 [6]-gingerol 
• 72749-01-0 (R)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one 
• 2380-78-1 homovanillyl alcohol 
• 61871-71-4 1-(4-hydroxy-3-methoxyphenyl)decane-3,5-dione 

Relevant articles and documents

Discovery and Characterization of Pure RhlR Antagonists against Pseudomonas aeruginosa Infections

Pseudomonas aeruginosa (P. aeruginosa) is an opportunistic human pathogen that forms biofilms and produces virulence factors via quorum sensing (QS). Blocking the QS system in P. aeruginosa is an excellent strategy to reduce biofilm formation and the production of virulence factors. RhlR plays an essential role in the QS system of P. aeruginosa. We synthesized 55 analogues based on the chemical structure of 4-gingerol and evaluated their RhlR inhibitory activities using the cell-based reporter strain assay. Comprehensive structure-activity relationship studies identified the alkynyl ketone 30 as the most potent RhlR antagonist. This compound displayed selective RhlR antagonism over LasR and PqsR, strong inhibition of biofilm formation, and reduced production of virulence factors in P. aeruginosa. Furthermore, the survival rate of Tenebrio molitor larvae treated with 30 in vivo greatly improved. Therefore, compound 30, a pure RhlR antagonist, can be utilized for developing QS-modulating molecules in the control of P. aeruginosa infections.

MnO2as a terminal oxidant in Wacker oxidation of homoallyl alcohols and terminal olefins

Efficient and mild reaction conditions for Wacker-type oxidation of terminal olefins of less explored homoallyl alcohols to β-hydroxy-methyl ketones have been developed by using a Pd(ii) catalyst and MnO2 as a co-oxidant. The method involves mild reaction conditions and shows good functional group compatibility along with high regio- and chemoselectivity. While our earlier system of PdCl2/CrO3/HCl produced α,β-unsaturated ketones from homoallyl alcohols, the present method provided orthogonally the β-hydroxy-methyl ketones. No overoxidation or elimination of benzylic and/or β-hydroxy groups was observed. The method could be extended to the oxidation of simple terminal olefins as well, to methyl ketones, displaying its versatility. An application to the regioselective synthesis of gingerol is demonstrated.

6-gingerol derivative and its preparation and application

A 6-gingerol derivative and its preparation and application are provided. That derivative has the following structure. The derivative of the present invention has antitumor activity and inhibit effect on tumor cells. In addition, the chemical properties o